Passing Ships
by hyper13
Summary: While traveling with the Obama campaign, Jess and Rory have a chance meeting. (that time when she did the Riverdance on his heart; that time that isn't a scene he replays over and over on nights when he can't sleep: 'I thought everything was fixed' 'Everything but him'). Literati.


Most days, the noise of the bar acted as white noise, like a sound machine, something to fill the background while he worked. When writing or reading, Jess could ordinarily tune out anything. This particular evening, however, he was stuck. At some point, he had hit a wall, and the words weren't coming, which meant that the particularly loud group gathered behind him were grating on his nerves.

Jess turned, intending on saying something to the lot of them, and that's when he saw _her_.

In the last year or so since he last saw her, there have been many times where Jess thought that he saw Rory Gilmore, only for it to be a trick of the light or for it to be some other slim brunette passing in his peripheral.

_(that time when she did the Riverdance on his heart; that time that isn't a scene he replays over and over on nights when he can't sleep: 'I thought everything was fixed' 'Everything but him')._

If this was a figment of his imagination, Jess was incredibly impressed.

Sitting in the corner of the group she was gathered with, Rory was curled up with a book, the rest of the world tuned out. Jess recognized the title, and the corner of his lips quirked up. It wasn't that good, certainly not his best work, but her copy looked well-read. The binding was creased, the cover and pages worn. He wondered how many times Rory had read _The Subsect_. More than it deserved.

Jess didn't realize he'd been staring at Rory until she glanced up, meeting his eyes as if she could feel his gaze on her. It was too dangerous to get caught up with Rory Gilmore again, but as he lifted his hand to pack up his stuff, Jess waved instead. She tucked a finger in the book to mark her page, giving him a wave in return with her free hand. Neither of them moved. After what happened last time, he's not even sure what he would say to her.

_(funny how the Riverdance music that plays in Jess's head sounds a lot like 'I'm in love with him. Despite all the bad he's done, I can't help it. I'm in love with him' playing to an obnoxious beat. Over and over and over again)._

He isn't entirely sure how long they stay like that, eyes locked, but the moment is cut off when someone nudges Rory in the arm. Her group is leaving. It isn't until then that Jess bothers to wonder what she's doing in Philadelphia, and what she's doing with this obnoxious group of people. Rory pulls her gaze from Jess and says something to the woman vying for her attention. Jess uses the moment to remember how to breathe and scan the bar for the jerk with a Porsche, but Richie Rich is nowhere in sight.

Rory tucked a bookmark into her book, slipping the book into her purse. She pulled on her coat, shoved her hands into her gloves, before sparing him another glance. Jess knows her. He knows her better than anyone. She hurt him the last time, so even though his traitorous hand waved at her, the fact that he hadn't moved to go talk to her spoke volumes.

She wasn't going to invade his space when he clearly didn't want her there. She thought he didn't want to talk to her.

And he didn't.

The corner of her lips turned up in a small smile, which he returned, and then she was gone out the door swept up in the drunken group, all talking over one another.

Honestly, he didn't.

As soon her group was gone, the sounds of the bar quieted significantly. Maybe he could finally get some work in. Jess turned his attention back to his laptop, settling his hands over the keys, willing the words to come.

Didn't he, though?

With a grunt of annoyance, Jess slammed the laptop shut, stuffing it and his scribblings into his bag as he ran for the door. Maybe he had taken too long. Maybe he should just run back inside and give up the whole thing. Maybe...

There she was, standing on the corner of the street, waiting to cross.

_He didn't._

Jess stared for a moment, then he headed that way. As the cross signal turned green, he called her name. "Rory!"

She and a few others from her group stopped. The rest drunkenly staggered across the street. Rory said something to those that waited for her. It must have been an assurance of sorts because, after a last glance at Jess, they crossed the street as well, leaving her alone on the corner. She didn't move. When he finally reached her, the small smile was back in place. "Jess."

"You're in Philadelphia."

"So I am."

Jess wondered if she ever thought about the last time that she was in Philadelphia. He wondered if she was thinking about it right now.

_(it's not like he thinks about it at least once a week, sometimes more. It never crosses his mind. 'I'm so sorry that I came here' 'I'm not. It's what it is. You, me.')_

"Friends of yours?" He gestures to the pack of drunks, and she follows his gaze. He kind of hoped not, the way they casually abandoned her on a street corner with a stranger.

Shrugging, Rory turns back to look at him. "Colleagues, more like."

It dawns on him, then. As much as he tries to avoid news of Rory, Luke has managed to share. She's traveling with the Obama campaign. Now she's here, in Philadelphia with them. Now he knows why the asshole isn't with her. "How long are you here?"

"Another week or so." She tugs on the ends of her sleeves, a nervous habit. It's endearing, and he wants to take her hands like he did so many years ago. "I would have told you, but..." Rory trails off, and Jess arches a brow at her. After a beat, she continues, "Things didn't go well for us the last time that I was here."

Jess says nothing. What is he supposed to say to that? It most certainly did not go well for him. He supposed, in the sense that she was riddled with guilt, it did not go great for her. Only, he was the one with the broken and damaged heart, torn again at the places she'd once mended.

The silence, coupled with the uncomfortable topic, is enough to spur on an outpouring of words, treating him to a real Gilmore ramble. "I didn't even know if you'd want to see me after what happened, after what I did to you. It wasn't fair, you didn't deserve that." For the record, as terrible as he had been in his teenage years, she was right. He didn't deserve that.

_('You came here alone, to Philadelphia.' 'He was out of town.' 'I don't deserve this, Rory' even he, filled with some real self-loathing tendencies knew that)._

"I didn't want to just expect that you'd want to see me, that you would want to. I walked by the publishing house like five times yesterday." Another instance where Jess's imagination hadn't been playing with him. He only caught her the one time; otherwise, he might have... well, it was hard to say what he would have done if Jess had realized it was her. Considering he was standing here talking to her when he should be in the bar trying to write, Jess had a reasonably good idea what he would have done had he noticed her. Rory was still rambling, "-and I'm sorry. I was sorry when it happened, and I've been sorry ever since."

"I know."

"It wasn't fair, and it is something I regret every day."

"Rory, seriously, it's okay. I forgive you."

She blinked at him. Rory had always been better at punishing herself than anyone else. He knows her, remember? "What?"

Jess shrugged. It had stung, it was a painful memory, and he wished it had played out differently, but ultimately he doesn't hold it against her. Everyone had to make dumb mistakes, mess up sometimes. His mistakes happened when he was in high school; hers just happened to come later. "I forgive you. It happened, it's in the past; there's no sense in reliving it."

"But-"

"Rory, let it go." He shoved his hands in his pockets, staring at her. "So, you're in Philly."

There was a beat where it looked like she might argue with him, then she said, "So I am." They had come full circle, but something in Jess's chest opened up; it felt like there had been a full ache there that he hadn't really been aware of it until it was gone.

"How's the boyfriend?"

She blinked at him, then understanding registered. "Logan? He proposed at graduation."

It was amazing how a person could feel simultaneously proud (she graduated Yale!) and devastated (the Riverdance playing in his head had a new refrain, though. A little change was good, after all. Right?). Jess was wrecked by a single sentence. Then again, it wasn't the first time.

He dropped his hand to her gloved hand, trying to recall if he'd been able to see a shiny rock on her finger in the bar. The lighting hadn't been great, and they weren't sitting close, but he thought he might have noticed a sparkling diamond. Coming from _Logan,_ it was bound to be overpriced and likely to blind a person.

_(Still: 'I'm in love with him.' - why would she say no?)._

He tries to find something to say, anything. Something witty; he's always got a quip on the tip of his tongue, but not today. Today he has nothing left to give. "Anyway, I can't really tell you how he's doing." There it is, a sliver of hope, a lifeline. Jess clings desperately to it. After what happened the last time, he should be more careful.

_(that kiss felt like they were finally in the right place like they had finally aligned. Jess finally had his life together, he was finally right for her. Turned out she hadn't been in the right place)._

He should be wearier but he can't. That hope is the only thing keeping him standing in this spot right now.

"Oh?"

"Well, when I said no, it was kind of the end of our relationship."

Jess searches her face, looking for any kind of... Something. Regret. Deception. He found neither. "Huh."

Rory nodded. "Everything's fixed," she said firmly. Jess recalled the last time she had said that, and he nodded.

It was a little hard to believe, but Jess was slowly pulling himself up that lifeline and out of a position of drowning. Luke had failed to mention that she was no longer with the boyfriend. Then again, Jess tended to run from the conversation when any topic of Rory was brought up. "Huh," he said again. The verbal thing still comes and goes.

She stared at him for a moment, rolling her shoulders. "I should..." she gestured the way her drunken colleagues had disappeared too. "We have an early morning."

"Where are you headed?"

"Hotel is at the end of the block."

Jess nodded, pressing the button to cross the street. "I'll walk with you."

"Oh... Jess, you don't have-"

"Rory, it's late. You're in a strange city, and I'm not going to let you walk back to your hotel alone." His heart may be held together by loosely tied string, but he still has one. Not to mention, if something happened to Rory, Jess would never forgive himself. He's not a monster.

At first, walking side by side on the street is awkward. They walk in silence, and Jess-who thrives in silence with other people-feels nervous and uncomfortable. Rory asks what he's been reading, though, and it starts to feel normal. A little like old times, except now he has a bit of a beard, he's matured, and he's not sure what's going on with Rory really.

They talk books all the way until they're standing outside her hotel. "Now, you have to walk alone in the dark," she pointed out.

Jess shrugged. "I'll be alright." He can see the guilt, so he offered, "I'll send you an e-mail when I get home, so you know I didn't get mugged or something."

She hesitated, but then she nodded. They both start talking at the same time, stopped by the other. She cleared her throat, and Jess gestures for her to go first. He may be the published author, but she always had a better gift for the spoken word. "It was good to see you, Jess. You look... you look good."

"So do you, Rory." Despite the reminder of the last visit, it was good seeing her. "I'm glad we talked."

She nodded, turning to head inside, and Jess can't stand not knowing. "Why'd you turn him down?"

Rory paused, turning to face him. They're several feet apart, and he recalled another instance where he waited until the last moment to ask her what he needed to know.

_('Why'd you come?' 'Because you didn't say goodbye.')._

This is different, yet it's very much the same. The answer _matters_.

She takes a moment to respond, and he thinks that maybe she isn't going to answer. He's about to turn to leave when she finally speaks up. "It was all wrong." Jess arched a brow at her, and she took a few steps forward to continue. "I have this belief that people are meant to be in your life for a purpose, right? Some are intended to be more permanent than others. At the time, it's hard to understand why they aren't around anymore, like when my mom didn't marry Max, but he wasn't right for her, not ultimately. He was right for her at that moment, and she gained something that she needed from that relationship, but he wasn't meant to be a permanent fixture in her life. Dean was what I needed when we were dating. He was nice, and he was safe, but he wasn't meant to be forever, and I was convinced that he was until you came along."

Jess had a clear idea of what his lesson in Rory's life was meant to be. "There was something for me to gain from being with Logan, at that moment, but..." she trailed off, glancing past Jess for a moment. "It was all wrong." He still didn't quite follow, but he could tell she wasn't done, so he waited. "Logan taught me to live a little more, to try new things, to be open to possibilities, but I don't want his life. I don't want to be Mrs. Huntzberger, managing the house while my husband goes off to work. I love her dearly, but I don't want to be my grandmother. I want to write; I want to write news and guest articles. I want to work, be my own person; I don't want to fade into the background and become a society wife. I... you got me back into school, you set me back on the right path. You were right when you came and said that all that wasn't me, and I'll forever be grateful to you for that because I didn't realize how lost I was until you showed up." She laughed as something occurred to her, "a little like how I was with Dean."

Jess could agree with her there. He never understood what she was doing with Dean once he got to know her. She'd been stuck in that safety net, afraid to leave that nest without a little push. Still, he wondered what this had to do with Richie Rich, and her refusing his proposal. It was often like this with Rory, though. She'd go off, and you would think it would have no relevance, and just when she was losing you, she'd get there.

Jess was always along for the ride.

"When Logan proposed, I realized a lot of that, a lot of what I didn't want. I could see my whole future laid out in front of me, and I didn't want it, not that one."

"I thought you loved him."

"I thought I did, too." She shrugged, holding her wrist with one hand. "I thought I loved Dean once, too." Jess nodded; he'd born witness to that firsthand.

_('And I'm not going to pine. I hope you didn't think I was going to pine, okay? I think... I think I may have loved you, but I just need to let it go. So, that's it, I guess.')_

Jess can't help but notice that she leaves out his name from the list of people she thought she once loved. "Anyway, I was just... filling a whole with Logan. He was playing his part in my life, and me in his. And that was it. Marrying him would have been wrong. Staying with him would have been wrong."

Jess nodded. It was a better answer than he could have hoped for. Maybe she had needed to come to that realization on her own, but she eventually got there, and Jess was glad for that. The one time he had met Logan, it had been enough for Jess to know that he didn't treat Rory right, and she was wasting her time with him. "Guess you have it all figured out, then."

She laughed, shaking her head. "Not quite, but I have a better grasp on what I want, what I need, and what I'm doing."

It was his turn to nod. "Back on track, then."

"Back on track," she agreed. Her gaze lingered on Jess, and he resisted the urge to squirm under it. It had been a long time since that kiss, but he still remembered what it felt like to hold her. He thought maybe he was getting to redo their last encounter, that she was finally in the right space, and so was he. Perhaps it was finally the right time for them to get it right.

He thinks about that. Then he thinks about how he hurt her, and Rory hurt him.

He thinks about him begging her to go away with him, anywhere, and how that probably wasn't the best way to do it, because she was meant to finish Yale and he had more growing to do.

_(he doesn't think about how even knowing that it still stings that she said no. 'Only say no if you really don't want to be with me.' 'No.'; it had crushed him, but he believed she had herself convinced of a lie)._

They might have missed their moment. It had come and gone, and both Jess and Rory had ruined their opportunities to try again. It was also entirely possible that this was it, their last shot to be together, to get it right. It was hard to say.

"I'll e-mail you when I get home," he said.

Rory nodded. "Please do." She pulled a scrap of paper out of her bag, scribbling on it. "Here." He glanced at it, smiling at the familiar handwriting. "That's the e-mail I check most regularly." She rocked on her feet, "so."

"Thanks."

* * *

It's the first thing he did when he got home. Jess ignored his roommates and headed up the stairs to his room, shutting himself away. It's a short e-mail that just informed her that he was not mugged, kidnapped, or otherwise harmed on his short walk back to his car, and he made it back in one piece.

Rory replied a few minutes later, as he was busy sorting through the mess he made of his notes when he decided to chase after her.

'_Jess,_

_You joke, but safety is important! At any rate, I'm glad to have run into you. I almost regret not walking into Truncheon on one of my first five attempts, but maybe it was better this way. It was Fate, just as it was one afternoon in New York City..._

_Anyway, I've missed you. I just... I thought you should know that because we spent a lot of time when our paths have crossed, not saying the things that were on our minds. So, you should know that I have missed you, and now you know. So, I'll just leave it at that. Don't be a stranger if you can help it._'

He read the e-mail several times before typing out a reply. Jess had thought, maybe, when he left her in that hotel lobby that it would be like the last time: their previous encounter for a year or more until they had another chance run-in. Her e-mail had proven him wrong. Rory had extended the line of communication to remain open, and this time, he wasn't going to disappoint.

It wasn't until several months later, after e-mailing daily, that Jess realized that they might not have missed their timing. Sure, she was still traveling with the campaign, and he lived in Philadelphia. But he had matured, leveled out; he wasn't so angry. She, too, had grown. Her expectations weren't quite so high, and she wasn't involved with anyone else.

It would take some work, a lot of planning, and it would probably take some compromise, but they were finally on equal footing. The next time he knew she was going to be in Stars Hollow, Jess booked the next flight to Hartford.

* * *

Jess had planned on being showered and changed when he first saw Rory again, but he should have anticipated that she would be at Luke's. He also probably should have called ahead to see if it was alright to stay in his uncle's apartment, but seeing as Luke had moved in with Lorelai, he didn't think there would be an issue.

Lorelai is the one who caught sight of him first. One second she's talking a mile a minute, and the next, her blue eyes are locked onto him. "Jess!" It's Luke who called his name, though, but Jess can't look at him. At the sound of his name, Rory looks up, and they lock eyes.

She smiled, "hi."

Jess's hand tightens on his duffel bag, "Hi." He looks to Lorelai. She has to know that they've been talking because Rory tells her everything. "Hi."

Lorelai blinked, "Hi."

Feeling awkward, Jess finally turned his attention back to Luke. "Hi."

"Hi...?" It's so reminiscent of that first time that Jess wants to laugh. There's no way they've come this far to take that many steps backward.

"Am I the only one that just had a weird sense of deja vu?" Lorelai asked. Leave it to her to address the elephant in the room.

Luke shook his head, "No, but last time it was because they were..." he trailed off, looking between Rory and Jess. Jess watched as Rory turned a little pink.

They hadn't exactly talked about dating, or even mentioned it being a possibility. He knew her.

They were meant to be together, and he had known it from the first moment that he saw her.

"Are you two...?" Luke pointed between them, brows knit together.

Rory looked at Jess, and he stared back. "We're working on it," he said, holding his breath. He was making an assumption here, a bold one at that.

"Slow and steady," Rory agreed.

They were going to do things right this time. "Alright," Luke said, clearly pleased. "How long are you in town for?"

"Just the weekend," Jess hitched his bag up onto his shoulder. "Thanks for letting me stay in your apartment." He clapped Luke on the shoulder, heading for the curtain.

"But I didn't-" Jess ignored him, going up the stairs.

When he made it back down, Rory was gone. He couldn't help his disappointment. He thought, maybe, with what they had sort of just agreed to, she would stick around. Luke looked up from his order pad, "She said she'd be right back."

Jess nodded, debating. When he looked out the window, there she was, standing on the sidewalk. He went out to meet her, ready to tell her everything he'd been thinking about, everything he wanted for them. Rory launched herself into his arms, and then they were kissing.

There was a lot to figure out, a lot to discuss, and some work to be put in, but whatever else happens with them, at least they know that part still works.

_(The Riverdance song is replaced by a new, rock and roll tune that sounds a lot like 'I love you' and he can feel the needle pulling the thread tight on the cracked parts of his heart)._

It isn't perfect, but it's a start.


End file.
